16424-35-4

Basic information

• Product Name: 2-pentylidenecyclopentan-1-one
• Synonyms: 2-pentylidenecyclopentan-1-one;2-Pentylidenecyclopentanone;Cyclopentanone,2-pentylidene-;Einecs 240-477-4;Pentylidene-2-cyclopentanone
• CAS NO: 16424-35-4
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23344
• EINECS: 240-477-4
• Mol File: 16424-35-4.mol

Chemical Properties

• Boiling Point: 240.6 °C at 760 mmHg
• Flash Point: 96.7 °C
• Appearance: /
• Density: 1.001 g/cm³
• Vapor Pressure: 0.0376mmHg at 25°C
• Refractive Index: 1.544
• CAS DataBase Reference: 2-pentylidenecyclopentan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-pentylidenecyclopentan-1-one(16424-35-4)
• EPA Substance Registry System: 2-pentylidenecyclopentan-1-one(16424-35-4)

Safety Data

• Hazardous Substances Data: 16424-35-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 4248, 1978 DOI: 10.1021/jo00415a061

InChI:InChI=1/C10H16O/c1-2-3-4-6-9-7-5-8-10(9)11/h6H,2-5,7-8H2,1H3

Upstream product

• 936-52-7 1-(N-morpholino)cyclopent-1-ene 
• 110-62-3 pentanal 
• 120-92-3 cyclopentanone 
• 42558-01-0 2-(1-hydroxypentyl)-cyclopentanone 
• 1352617-33-4 2-pentylpent-1-enyl t-butyldimethylsilyl ether 
• 124-04-9 Adipic acid 

Downstream Products

• 4819-67-4 2-pentyl-cyclopentanone 
• 25564-22-1 2-pentyl-2-cyclopenten-1-one 
• 34687-45-1 2-pentenyl cyclopentanone 
• 16424-55-8 (E)-dec-5-enoic acid 
• 84168-28-5 (Z)-5-decenoic acid 
• 39647-11-5 <2S*,3R*>-3-methoxycarbonylmethyl-2-pentylcyclopentanone(methyl dihydroepijasmonate) 
• 51806-23-6 methyl 1-carboxymethyl-1-(2-pentyl-3-oxocyclopentyl)acetate 
• 24851-98-7 methyl 3-oxo-2-pentylcyclopentaneacetate 

Relevant articles and documents

Aldol Condensation of Cyclopentanone with Valeraldehyde Over Metal Oxides

Kinetics of the cross aldol condensation of valeraldehyde with cyclopentanone was investigated in a batch reactor under atmospheric pressure at 130?°C using heterogeneous metal modified oxides, such as CeO2–MgO, FeO–MgO, FeO–CaO as well as pristine CaO as catalysts. The catalysts were prepared either by evaporation impregnation or deposition precipitation methods and characterized by XRD, TEM, SEM, nitrogen adsorption, ammonia and CO2 TPD. The results revealed that an optimum amount of strong basic sites gives the highest ratio between cross condensation and self-condensation products of valeraldehyde. The highest yield of the desired product 2-pentylidenecyclopentanone (66%) was obtained with FeO–MgO prepared by the deposition precipitation methods. Graphical Abstract: Cross-condensation of valeraldehyde with cyclopentanone was investigated over heterogeneous Fe–CaO, CeO–MgO, FeO–CaO and CaO catalysts at 130?°C using cyclopentanone as a solvent and reactant. The highest yield of the desired product, 2-pentylidene-cyclopentanone, finding applications as fragrances, flavours and pharmaceuticals, was 66% obtained over FeO–MgO catalyst exhibiting both acid and basic sites.[Figure not available: see fulltext.].

Synthesis of Unsaturated Spiroacetals, Cyclopentanone Derivatives, in the Presence of Natural Aluminosilicate Modified with Zirconium Cations

Abstract: Conditions for the condensation of cyclopentanone and n-valeric aldehyde to 2-pentylidenecyclopentanone in the presence of an alcoholic solution of piperidine have been developed. The isomerization of the latter in a continuous-flow system over γ-Al2O3 yields 2-pentylcyclopent-2-en-1-one. The condensation of the obtained unsaturated ketones with ethane-1,2-diol in the presence of a heterogeneous catalyst, a natural aluminosilicate (perlite) modified with zirconyl sulfate, has been studied. The optimum conditions for the preparation of the corresponding unsaturated spiroacetals have been found. The synthesized compounds can be used as synthetic fragrances for different purposes.

Dihydro(dialkylamino)jasmonate compound or salt thereof

The invention relates to a dihydro(dialkylamino)jasmonate compound or salt thereof. The dihydro(dialkylamino)jasmonate compound is shown as a formula (1); the formula (1) is shown in the description;in the formula (1), n is an integer from 1 to 9; R1 is -CH3, -CH2CH3 or -CH2CH2CH3; R2 is -CH3, -CH2CH3 or -CH2CH2CH3. According to the dihydro(dialkylamino)jasmonate compound or the salt thereof, thestress resistance of plants can be remarkably improved and the yield is increased; the dihydro(dialkylamino)jasmonate compound or the salt thereof belongs to the technical field of organic synthesis,can be applied to a plant growth regulator and is convenient to use, so that the dihydro(dialkylamino)jasmonate compound or the salt thereof has an extremely wide application prospect.

Method for synthesizing (1R,2S)-methyl dihydrojasmonate

The invention discloses a novel method for synthesizing (1R,2S)-methyl dihydrojasmonate by using an asymmetric Michael addition reaction. The method comprises the steps: firstly, subjecting cyclopentanone, which serves as a starting raw material, to an aldol reaction with n-valeraldehyde under alkaline conditions to produce 2-pentylidene cyclopentanone 2, and then, carrying out double-bond transposition under acidic conditions, so as to obtain 2-n-pentyl-2-cyclopentenone 3; then, carrying out a Michael addition reaction with dimethyl malonate in the presence of a chiral amino-acid lithium salt, and carrying out silicagel-column chromatographic separation twice, so as to obtain (1S,2S)-2-n-pentyl-3-dimethyl malonate cyclopentanone 4; and finally, carrying out a hydrolyzed decarboxylation reaction, thereby obtaining (1R,2S)-methyl dihydrojasmonate. According to the method, the synthesis route is simple and direct, the reaction conditions are mild, and the target compound can be prepared by only four-step reactions.

Method of manufacturing methylcyclopentanone deriv. (by machine translation)

PROBLEM TO BE SOLVED: To provide an efficient method for producing a cyclopentanone derivative usable as an intermediate for a methyl (3-oxocyclopentyl)acetate derivative useful as a perfumery material.SOLUTION: The method for producing the cyclopentanone derivative expressed by general formula (III) comprises Michael addition reaction of a 2-cyclopenten-1-one derivative and an ester compound in the presence of a solid base catalyst containing a phosphazene base or a guanidine base. In the formula, Ris a 1-10C hydrocarbon group; Ris 1-4C alkyl; and Ris 1-4C alkyl or alkoxyl.

Synthesis of d-decalactone

The application and shortcomings of typical synthetic method of title d-decalactone was introduced in brief. A synthesis of 2-pentylidene cyclopentanone starting from cyclopentanone and n-valeraldehyde through aldol condensation, followed by dehydration, was studied and the yield reached 86.3 %. Then 2-pentenyl cyclopentanone was prepared in a yield of 91.5 % from 2-pentylidene cyclopentanone with a hydrogenation methodology under atmospheric pressure and use Pt/C as catalytic. Through Baeyer-Villiger oxidation, d-decalactone was synthesized in a yield of 61.2 %. Experiments by orthogonal experiment method to optimize the reaction conditions to determine the response of a reasonable process parameters and the analysis of the factors affecting the reactions. The structures and compositions of these compounds were accomplished by IR and GC-MS.

A highly selective aldol condensation of cyclopentanone with valeraldehyde over hydrotalcite-type catalysts

The aldol condensation using cyclopentanone with valeraldehyde was conducted at hydrotalcites catalysis. The catalyst was obtained by calcining the hydrotalcite precursor (Mg/Al = 3:1) at 773 K. Its reaction performance was evaluated on the various molar ratios of cyclopentanone to n-valeraldehyde. A good catalytic selectivity of 90 % and a high conversion of 93 % were achieved under mild conditions.

Oxidative conversion of silyl enol ethers to α,β-unsaturated ketones employing oxoammonium salts

The oxidative conversion of silyl enol ethers to α,β-unsaturated ketones using a less-hindered class of oxoammonium salts (AZADO +BF4-) is described. The reaction proceeds via the ene-like addition of oxoammonium salts to silyl enol ethers.

PROCESS FOR PRODUCING A 2-ALKYL-2-CYCLOALKENE-1-ONE

The present invention relates to a process for producing a 2-alkyl-2-cycloalken-1-one represented by the following general formula (2), including the step of reacting a 2-alkylidene cycloalkanone in the presence of a palladium and/or platinum catalyst which is treated in the following steps (a) and (b); and a method for activating the palladium and/or platinum catalyst including the following steps (a) and (b): Step (a): activating the palladium and/or platinum catalyst in an atmosphere containing a hydrogen gas; and Step (b): replacing the hydrogen gas being present as the atmosphere for the catalyst in the step (a), with an inert gas to remove the hydrogen gas out of the reaction system, wherein m is 0 to 3; n is 1 or 2; R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; and R3 is an alkyl group having 1 to 5 carbon atoms. In accordance with the present invention, the 2-alkyl-2-cycloalken-1-one can be produced with a high purity and a high productivity.

METHOD FOR PRODUCING OF 2-ALKYL-2-CYCLOALKEN-1-ONE

The present invention relates to [1] a process for producing a 2-alkyl-2-cycloalken-1-one represented by the following general formula (2), which includes the step of subjecting a 2-(1-hydroxyalkyl)cycloalkan-1-one to dehydration and isomerization in the co-existence of an acid and a platinum group metal catalyst, and [2] a process for producing an alkyl(3-oxo-alkylcycloalkyl)acetate which is useful as a perfume material, using the 2-alkyl-2-cycloalken-1-one: wherein n is an integer of 1 or 2; and R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms with the proviso that R1 and R2 may form a ring through a carbon atom adjacent thereto.